JP3234004B2 - Disperse dye mixture - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a disperse dye mixture which is particularly excellent in both light fastness and temperature dependency and can dye polyester fibers in a good orange to reddish blue color. The present invention relates to a dye mixture containing yellow and blue disperse dyes.

[0002]

2. Description of the Related Art Conventionally, as a material of an automobile seat,
Although cloth made of polyester fiber is often used,
In recent years, as the interior of automobiles has been fashioned, colorful seats have been required. But,
In the case of a sheet for an automobile, the sheet is often exposed to direct sunlight at a high temperature in a closed room, so that the sheet tends to fade, and it is difficult to maintain a beautiful color for a long time. Therefore,
As a dye for dyeing polyester fibers for automobile sheets, it is desirable to use a dye having both excellent durability fastness and temperature dependency.

However, conventionally, there are few dyes excellent in both light fastness and temperature dependency, and no satisfactory dye has been found as a dye for an automobile sheet. For example, the following compounds (a) to (d) contained in the structural formulas [3] and [4] of claim 2 are described in Examples 261, 121, 110 and 110 of JP-B-61-39347. Each of these dyes is known from Example 46, and these dyes alone are excellent in light fastness but insufficient in dyeing temperature dependency and dyeing property.

[0004]

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On the other hand, a disperse dye having good light fastness and sublimation fastness as a single product is exemplified by the following structural formulas (e) to (e).
Dyes such as (g) are known. However, for practical colors such as brown color and gray color prepared by mixing a yellow disperse dye of the following structural formula (e), a red disperse dye of the following structural formula (f), and a blue disperse dye of the following structural formula (g): Are extremely poor in light fastness, and a mixture which does not deteriorate in light fastness even when mixed is desired.

[0006]

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[0007]

SUMMARY OF THE INVENTION In view of the above circumstances, the present inventors have provided a disperse dye which is excellent in light fastness and temperature dependency and suitable for dyeing polyester fibers for automobile sheets. As a result of various studies as objectives, it has been found that the specific dye mixture of the present invention achieves the above objects.

[0008]

SUMMARY OF THE INVENTION In view of the above circumstances, the present inventors have determined that the orange-reddish blue disperse dye represented by the above formula (1) has excellent temperature fastness while maintaining excellent light fastness. As a result of conducting various studies on a method for improving dyeing properties,
It has been found that when the dye of the above formula [1] and the orange to reddish blue dye of the above formula [2] are mixed and used, the dyeing properties are remarkably improved as compared with the case of single use. completed.

That is, the first aspect of the present invention is the above-mentioned formula [1]
0.1 to 10 based on the monoazo dye represented by
It exists in a disperse dye mixture obtained by blending a monoazo dye represented by the above formula [2] by weight. When R ¹ and R ^{2 in} the above formulas [1] and [2] are both a hydroxyethoxyethyl group, surprisingly, R ^{1 in} the above formula [1] is a hydroxyethoxyethyl group. In the mixture of the monoazo dye represented by the formula [3] and the monoazo dye represented by the formula [4] in an amount of 20 to 40% by weight. It was found that the dyeing properties were remarkably improved when the content was within the above range, and the present invention reached the second invention.

That is, the second invention of the present application is based on the above formula [3]
Is present in a disperse dye mixture comprising a monoazo dye represented by the formula [4] and a monoazo dye represented by the formula [4], which is 1.5 to 4 times the amount of the dye. Furthermore, the above formulas [1] and [2]
To the orange-reddish blue disperse dye mixture obtained by blending the monoazo dye of the formula [5]

The disperse dye mixture containing the yellow disperse dye of [9] and the blue disperse dye of the above formulas [10] to [12] was found to have excellent light fastness, and reached the third invention of the present application. .

That is, the third invention of the present application relates to a monoazo dye represented by the formula [1],
A disperse dye mixture obtained by blending the monoazo dye represented by the formula [2] by weight or the monoazo dye represented by the formula [3] 1.5 to 4 times the weight of the dye to the monoazo dye represented by the formula [3]. [4]
Is added to 100 parts by weight of a disperse dye mixture obtained by blending a monoazo dye represented by

One or more yellow disperse dyes 2 to 200 selected from the group consisting of [9]
0 parts by weight and one or two or more blue disperse dyes selected from the group consisting of the above formulas [10] to [12].
0 parts by weight are present in the disperse dye mixture.

Hereinafter, the present invention will be described in detail. In the first invention of the present invention, the disperse dyes represented by the above formulas [1] and [2] are mixed and used.
The dye of the formula [2] is used in an amount of 0.1 to 10 with respect to the dye of the formula [1].
It is by weight, preferably 0.3 to 4 times by weight. Equation [2]
If the amount of the dye is too small or too large, the effect of improving dyeing properties and temperature dependence is small.
The dye represented by the formula [2] to be mixed with the dye of the formula [1] may be a single dye or a mixture of the dyes represented by the formula [2].

In the above formulas [1] and [2], X is a nitro group, a cyano group, a methylsulfonyl group or a halogen atom. As the halogen atom, a chlorine atom or a bromine atom is preferable. X is particularly preferably a nitro group. Y and Z are a hydrogen atom, a cyano group, a nitro group, a trifluoromethyl group, a halogen atom or a methylsulfonyl group. Y and Z may be the same or different from each other. As the halogen atom represented by Y and Z, a chlorine atom or a bromine atom is preferable. In particular, a combination of X as a nitro group, Y as a cyano group, and Z as a hydrogen atom is preferable. W is a hydrogen atom, a halogen atom, a C ₁ -C ₂ alkyl group or an alkoxy group, and particularly preferably a hydrogen atom.

R ¹ and R ² each independently represent a C ₁ -C ₄ alkyl group or cyano group, a halogen atom, a hydroxy group, a hydroxyalkoxy group, a C ₁ -C ₄ alkoxy group, a hydroxyalkoxyalkoxy group, an acyloxyalkoxy group, It is a C ₂ -C ₄ alkyl group substituted with an acyloxyalkoxyalkoxy group or an alkoxyalkoxy group. Specifically, examples of the C ₁ -C ₄ alkyl group include a methyl group, an ethyl group, a linear or branched propyl group and a butyl group, and a C ₂ -C 4 substituted with a cyano group, a halogen atom or a hydroxy group. ₄ Examples of the alkyl group include a cyanoethyl group, a chloroethyl group, a bromoethyl group, a hydroxyethyl group, a cyanopropyl group, a chloropropyl group, a bromopropyl group, a hydroxypropyl group, a hydroxybutyl group, and the like.
Hydroxy alkoxyalkoxy group, acyloxyalkoxy group or acyloxyalkyl alkoxyalkoxy hydroxyethoxy ethyl group as C ₂ -C ₄ alkyl group substituted with a group, hydroxyethoxy butyl group, hydroxypropoxy ethyl, hydroxypropoxy propyl, hydroxyethyl butoxyethyl group A hydroxyethoxyethoxyethyl group, a hydroxypropoxypropoxypropyl group, a formyloxyethoxyethyl group, an acetyloxyethoxyethyl group, a propionyloxyethoxyethyl group, an acetyloxypropoxypropyl group,
An acetyloxypropoxypropoxypropyl group can be exemplified, and as the C ₂ -C ₄ alkyl group substituted with C ₁ -C ₄ alkoxy, a methoxyethyl group, a butoxyethyl group, an ethoxypropyl group, a propoxypropyl group, and a methoxybutyl group are exemplified. It can, alkoxyalkoxy the C ₂ -C ₄ alkyl group substituted with a group methoxyethoxy propyl group, and an ethoxy ethoxyethyl group can be exemplified.

The second invention of the present invention relates to the above-mentioned formulas [1] and [2], particularly when both R ¹ and R ² are hydroxyethoxyethyl groups, that is, the formulas [3] and [4] When using a mixture of disperse dyes,
A particularly preferred mixing ratio is 1.5 to 4 times the dye of the formula [4] with respect to the dye of the formula [3]. In the range of the mixing ratio, the dyeing property and the temperature dependency are particularly improved.

On the other hand, as described above, the third invention of the present invention relates to an orange-reddish blue disperse dye mixture comprising the monoazo dyes represented by the formulas [1] and [2]. Expressions [5] to

It comprises a yellow disperse dye [9] and a blue disperse dye [10] to [12]. In the compound represented by the formula [5], R ⁵ is specifically:
_{-C 2 H 4 OH, -CH 2} CH (CH 3) OH, -C 3
_{H 6 OH, -C 2 H 4} CN, represents a -C ₃ H ₆ CN, in _{particular, -C 2 H 4 OH, -C} 2 H 4 CN are preferred.

In the compounds represented by the above formulas [6] and [10], examples of the halogen atom represented by R ⁶ or R ¹⁰ include a fluorine atom, a chlorine atom and a bromine atom. Atoms are preferred. Previous expression [8]
Specific examples of R ^{8 in} the compound represented by are methyl group, ethyl group, (n) -propyl group, i-propyl group, -C ₂ H ₄ OH, -CH ₂ CH (CH ₃ ) OH,-
_{C 3 H 6 OH, -C 2} H 4 CN, include -C ₃ H ₆ CN group, in _{particular, -C 2 H 4 OH, -C} 2 H 4 CN group.

[0018]

In the compound represented by [9] or [12], the C ₁ -C ₂ alkyl group represented by R ⁹ or R ¹² is a methyl group or an ethyl group. In the above formula [10], the hydroxy C ₂ -C ₃ lower alkyl group of R ¹⁰ represents a hydroxy lower alkyl group such as —C ₂ H ₄ OH and —C ₃ H ₆ OH, and especially —C ₂ H ₄ OH is preferred.

In the above formula [11], R ¹¹ is -C ₃ H ₆
A lower alkoxy lower alkyl group such as OCH ₃ and —C ₃ H ₆ OC ₃ H ₇ , or —C ₂ H ₄ OC ₂ H ₄ OC
Lower alkoxy lower alkoxy lower alkyl groups such as ₂ H ₅ and —C ₂ H ₄ OC ₂ H ₄ OCH ₃ are exemplified, but lower alkoxy lower alkyl groups are preferable. Third of the present invention
The mixing ratio of the disperse dye mixture in the invention of the invention is based on 100 parts by weight of the orange to reddish blue disperse dye mixture obtained by blending the monoazo dyes represented by the formulas [1] and [2] with the formula [ 5] No

One to two or more yellow disperse dyes selected from the group consisting of [9] are used in a total amount of 2 to 2,000.
Parts by weight, preferably 10 to 1000 parts by weight, and a total of 2 to 2000 parts by weight of a total of one or more blue disperse dyes selected from the group consisting of the above formulas [10] to [12], preferably 10 to 1000 parts by weight.

The most preferred mixing ratio is 30 to 500 parts by weight of the yellow disperse dye and 30 to 5 parts of the blue disperse dye, based on 100 parts by weight of the orange to reddish blue disperse dye mixture.
00 parts by weight. The disperse dyes represented by the above formulas [1] and [2] can be produced according to the method described in JP-B-61-39347. As a compounding method, a dye having a single structure can be mixed to obtain a mixed dye, but it can also be obtained by mixing two or more kinds of coupling components at the time of dye synthesis and performing a coupling reaction. .

The disperse dyes [5] to [12] are also known per se, and can be produced according to a known method. Fibers which can be dyed with the disperse dye mixture of the present invention include polyethylene terephthalate, terephthalic acid and 1,4-
Polyester fibers, such as polycondensates with bis- (hydroxymethyl) cyclohexane, or cotton, silk,
Blend products and blended products of the above-mentioned polyester fibers and fibers such as wool, rayon, polyamide, and polyurethane can be used. In particular, when the fiber is a polyester fiber for an automobile seat, the polyester fiber having a thickness of 2 to 5 deniers is
In the case of fine denier polyester fabric for clothing, polyester fibers having a thickness of 0.1 to 1 denier are preferred.

In dyeing polyester fibers using the disperse dye mixture of the present invention, the disperse dye mixture of the present invention is insoluble or hardly soluble in water. Therefore, naphthalenesulfonic acid and formaldehyde are used as dispersants in a conventional manner. A dye bath or printing paste dispersed in an aqueous medium using a condensate, higher alcohol sulfate, higher alkyl benzene sulfonate, or the like, can be prepared, and can be dyed or printed.

For example, in the case of dip dyeing, if a normal dyeing method such as a high temperature dyeing method, a carrier dyeing method or a thermosol dyeing method is applied, a polyester fiber or a blend thereof can be dyed with excellent fastness. it can. that time,
In some cases, even better results can be obtained by adding known acidic substances such as formic acid, acetic acid, phosphoric acid or ammonium sulfate to the dyeing bath. The pH of the dyeing bath is usually 5.
It is preferable to adjust it in the range of 0 to 9.5. The dyeing temperature is, for example, about 120 to 140 ° C.

In particular, the mixture of the disperse dyes of the above formulas [3] and [4] exhibits particularly excellent dyeing properties and temperature dependency when applied to the exhaust dyeing method. The dyeing conditions in the exhaust dyeing are not particularly limited. For example, the dyeing temperature is 120 to 140.
C., the dyeing time is about 30 to 60 minutes, and the pH of the dyeing bath is about 4.0 to 9.5.

In dyeing, various leveling agents and / or ultraviolet absorbers may be used in combination.

[0026]

EXAMPLES Next, the present invention will be described more specifically with reference to examples, but the present invention is not limited to the following examples. Examples 1 to 17 and Comparative Examples 1 to 17 Red disperse dyes [1-1] to [1 to 12] described in Table 1 below or [2-1] to [2] described in Table 2 below. 12]
Red disperse dye alone or 1 g of a dye mixture obtained by mixing the dyes described in Table 1 and the dyes described in Table 2 in the proportions described in Table 3 was used in an amount of 1 g of a naphthalenesulfonic acid-formaldehyde condensate. 100 g of polyester fiber is immersed in a dye bath prepared by dispersing in 3 liters of water containing 2 g of higher alcohol sulfate,
After dyeing for 0 minutes, soaping, washing with water and drying were performed, and a red dyed cloth was obtained. The light fastness, sublimation fastness and water fastness of the obtained dyed fabric, as well as the temperature stability and the pH stability during dyeing of the dye, were all good.

Further, the dye dyed on the dyed cloth was dissolved and extracted with a dimethylformamide solution of 0.1% phosphoric acid and colorimetrically determined. Example No. 1 The dyeing dye concentration (relative value) of each dyeing cloth of each example was calculated with the dyeing concentration in 1-1 as 100 (reference), and is shown in Table-3. The dyeing dye concentration was similarly calculated for dyed fabrics dyed under the same dyeing conditions except that the dyeing temperature was 120 ° C., and the temperature dependency was determined according to the following formula. The results are shown in Table-3.

[0028]

## EQU1 ## Temperature dependency (%) = (Dyeing dye concentration at 120 ° C. × 60 minutes dyeing / 130 ° C. × Dyeing dye concentration at 60 minutes dyeing) × 100

[0029]

[Table 1]

[0030]

[Table 2]

[0031]

[Table 3]

[0032]

[Table 4]

[0033]

[Table 5]

Examples 18 to 23 and Comparative Example 18 [1-1] (included in formula [3] above) and No. 2 in Table-2. Using each red disperse dye of [2-1] (included in the above formula [4]), the mixing ratio is shown in Table 1.
Except having set the ratio of 4, it was the same as Examples 1-17. The results are shown in Table-4.

As can be seen from Examples 18 to 20, in the case of the disperse dyes of the above formulas [3] and [4], the mixing ratio is 1:
In the range of 1.5 to 4, the dyeing property and the temperature dependency are remarkably improved.

[0036]

[Table 6]

Example 24 No. 2 in Table 1 [1-1] 25 parts by weight of the monoazo dye and No. 1 in Table-2. To 60 g of the disperse dye mixture comprising 75 parts by weight of the monoazo dye of [2-1], 140 g of ligninsulfonic acid formalin condensate and 650 g of water were mixed, wet-pulverized with a sand grinder, and spray-dried. 0.08 g of a nonionic leveling agent (Diaserver (registered trademark) LR-PSL: manufactured by Mitsubishi Kasei Corporation) was added to 0.07 g of the powdery disperse dye mixture, and an ultraviolet absorber (trade name: Sunlife LP-100: 0.10 g of Nika Chemical Co., Ltd.)
150 ml of water was added to adjust the pH of the dyeing bath to 5.5, and 5 g of a polyester fabric was put into the bath and subjected to exhaustion dyeing at 130 ° C. for 1 hour, then soaped, washed with water and dried to obtain a red dyed cloth.

The light fastness of this dyed cloth is based on a test method specified in JIS (JIS L-0843) and modified for automobiles (temperature is 89 ° C. ± 5 ° C.), and a flexible polyurethane foam is provided on the back side of the test cloth. (10 mm) and determined by a discoloration scale specified by JIS). Example 25 Powdery disperse dye mixture produced according to Example 24
150 ml of water was added to 2 g, and the dyeing bath was adjusted to pH 7,
5 g of fine denier polyester fabric (0.8 denier in thread thickness) was added thereto, and exhaust dyeing was performed at 135 ° C. for 60 minutes, and then reduction washing, water washing and drying were performed according to a conventional method to obtain a red dyed fabric. . The light fastness of this product was class 6 (J-L0843 method, 40 hours).

Examples 26 to 59 and Comparative Examples 26 to 59
(Comparative Examples 19 to 25 are next numbers.) The orange-reddish blue system shown in Table-5 and the disperse dyes were used alone or in the proportions shown in Table-5. Staining and evaluation were performed in the same manner as in Nos. 1 to 17. The light-fastness, sublimation fastness, and water fastness of the obtained dyed fabric, as well as the temperature stability and the pH dependency during dyeing, were all good. Table 5 shows the dyeing concentration and temperature dependency obtained in the same manner as in Examples 1 to 17. In addition,
In Table-5, for example, No. M-Br in the W column of 28 is B
It indicates that r is substituted at the m-position with respect to the amino group of the phenylamino group.

[0040]

[Table 7]

[0041]

[Table 8]

[0042]

[Table 9]

[0043]

[Table 10]

[0044]

[Table 11]

[0045]

[Table 12]

[0046]

[Table 13]

[0047]

[Table 14]

[0048]

[Table 15]

Example 60 Monoazo dye 25 represented by the following structural formula [1-60]
% Of a disperse dye mixture comprising 75% by weight of a monoazo dye represented by the following structural formula [2-60]

[0050]

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To 60 g, 140 g of ligninsulfonic acid formalin condensate and 650 g of water were mixed, wet-pulverized with a sand grinder, and spray-dried. A nonionic leveling agent (Diaserver (registered trademark) LR-PSL: manufactured by Mitsubishi Kasei Co., Ltd.) was added to 0.09 g of the powdery disperse dye mixture in an amount of 0.1 g.
08g, UV absorber (trade name: Sunlife LP-10)
0: 0.10 g of Nika Chemical Co., Ltd.) and 150 ml of water were added, and the dyeing bath was adjusted to pH 5.5. 5 g of polyester fabric was added thereto, and exhaust dyeing was performed at 130 ° C. for 1 hour. Next, the fabric was soaped, washed with water and dried to obtain a blue-red dyed cloth.

A test method in which the light fastness of this dyed cloth was modified for automobiles based on the test method specified in JIS (JIS L-0843) (at a temperature of 89 ° C. ± 5 ° C., and a soft polyurethane foam was placed on the back side of the test cloth. (10 mm) and determined by a discoloration scale specified by JIS).

Example 61 Powdery disperse dye mixture produced according to Example 60
150 ml of water was added to 5 g to adjust the dyeing bath to pH 7,
5 g of fine denier polyester cloth (0.8 denier in thread thickness) is put into this and dyed exhaustively at 135 ° C. for 60 minutes, and then reduced and washed, washed with water and dried according to a conventional method to obtain a blue-red dyed cloth. I got The light fastness of this product was class 6 (J-L0843 method, 40 hours).

Example 62 Yellow disperse dye 3 in which R ⁶ is H in the above formula [6]
0 g of the dye 40 represented by the structural formula [1-1] of Example 1
6 parts by weight of the dye 6 represented by the structural formula [2-1] of Example 1.
20 g of a red disperse dye mixture consisting of 0 parts by weight and the following structural formula [10-1]

[0055]

Embedded image

To a mixture of 18 g of the blue disperse dye represented by the formula above, 140 g of ligninsulfonic acid formalin condensate and 650 g of water were mixed, wet-pulverized with a sand grinder, and spray-dried. This powdery disperse dye composition 0.08
5 g of nonionic leveling agent (Diaserver (registered trademark))
LR-PSL: 0.08 g of Mitsubishi Kasei Co., Ltd .; 0.10 g of an ultraviolet absorber (trade name: Sun Life LP-100: Nika Chemical Co., Ltd.); 150 ml of water; .5, polyester cloth 5
g was added and dyed at 130 ° C. for 1 hour, then soaped, washed with water and dried to obtain a brown dyed cloth.

A test method in which the light fastness of this dyed cloth is modified based on the test method specified in JIS (JIS L-0843) for automobiles (temperature is 89 ° C. ± 5 ° C., and a soft polyurethane foam is provided on the back side of the test cloth. (10 mm) and determined by a discoloration scale specified by JIS). In addition, the sublimation fastness was grade 4 as a result of white polyester cloth sandwiched between dyed cloths and contacted at 180 ° C. for 30 seconds to determine contamination of the white cloth by gray scale.

Comparative Example 62 (Comparative Examples 60 to 61 are missing numbers) In the method of Example 62, only the red component is a red disperse dye mixture represented by the structural formulas [1-1] and [2-1] of Example 1. To disperse dye 9 represented by the above structural formula [f]
Dyeing was carried out in the same manner except that the amount was changed to 5 g to obtain a brown dyed cloth. When the evaluation was performed in the same manner as in Example 62, the light fastness was 2nd grade and the sublimation fastness was 3rd.

Examples 63 to 73 Polyester fabrics were dyed and evaluated in the same manner as in Example 62 except that the yellow disperse dye was changed to the dyes shown in Table 6 below. Table 6 shows the hue, light fastness and sublimation fastness of the dyed fabric.

[0060]

[Table 16]

[0061]

[Table 17]

[0062]

[Table 18]

[0063]

[Table 19]

Examples 74 to 80 Hue and lightfastness of a dyed cloth obtained by dyeing a polyester fabric in the same manner as in Example 62 except that the blue disperse dye was changed to the dyes shown in Table 7 below. And the sublimation fastness are shown in Table-7.

[0065]

[Table 20]

[0066]

[Table 21]

[0067]

[Table 22]

Examples 81 to 83 In Example 62, the mixing ratio (weight ratio) of the dyes of the structural formulas [1-1] and [2-1] in the red disperse dye mixture was changed as shown in Table 8 below. The polyester fabric was dyed and evaluated in the same manner as in Example 62 except for the above. The results are shown in Table-8.

[0069]

[Table 23]

Example 84 To 0.25 g of the powdery disperse dye composition produced in the same manner as in Example 62, 150 ml of water was added to adjust the dye bath to pH 8.2, and 5 g of fine denier polyester cloth (yarn 0.8 denier) and put at 135 ° C for 6
Exhaustion dyeing was performed for 0 minutes, followed by reduction washing, water washing and drying according to a conventional method to obtain a dark red dyed cloth. Its light fastness (J-L0843 method, 40 hr) was 6
Grade (blue scale).

Examples 85-88 Dyeing of polyester fabric was carried out in the same manner as in Example 62, except that the amounts of the yellow, red and blue dye components were changed to the proportions shown in Table 9 below. And evaluated. The results are shown in Table-9.

[0072]

[Table 24]

Example 89 The dye and the dye represented by the structural formula [1-1] in Example 62 were used.
And a red disperse dye comprising the dye represented by the structural formula [2-1]
In the above formula [1], X is -NO _Two, Y is
-CN, Z is H, R¹Is -C_ThreeH₆OC_TwoH_FourOC
H_Three, 40% by weight of a monoazo dye in which W is H and the above formula
In [2], X is -NO_Two, Y is -CN, Z is H,
R^TwoIs -C_ThreeH₆OC_TwoH_FourOCH_ThreeIs a monoazo dye
To 20 g of a red disperse dye mixture consisting of 60% by weight
Otherwise, the dyeing is performed in the same manner as in Example 62 to obtain a brown color.
Was obtained. Light fastness and rise simultaneously with Example 62
Hua fastness was evaluated. The results are shown in Table-10.

Comparative Example 89 (Comparative Examples 63 to 88 are missing numbers) Dyeing was carried out in the same manner as in Example 89 except that the red component was changed to 47.5 g of the disperse dye represented by the structural formula [F]. Thus, a brown dyed cloth was obtained.
Light fastness and sublimation fastness were evaluated in the same manner as in Example 62. The results are shown in Table-10.

[0075]

[Table 25]

Examples 90 to 96 The polyester fabric was dyed and evaluated in the same manner as in Example 89 except that the yellow disperse dye was changed to the yellow disperse dye described in Table 11. Table 11 shows the hue, light fastness and sublimation fastness of the dyed fabric.

[0077]

[Table 26]

Examples 97 to 100 The polyester fabric was dyed and evaluated in the same manner as in Example 89, except that the blue disperse dye was changed to the blue disperse dye described in Table-121. Hue of dyed cloth,
Table 12 shows the light fastness and the sublimation fastness.

[0079]

[Table 27]

Examples 101 to 108 The red disperse dye mixture [2-
13] was changed to the red disperse dye mixture described in Table 13 (compounding ratio [1]: [2] = 4: 6 (weight ratio)), and the polyester fabric was dyed and evaluated in the same manner as in Example 62. did. Table showing hue, light fastness and sublimation fastness of dyed fabric
FIG.

[0081]

[Table 28]

[0082]

[Table 29]

[0083]

[Table 30]

[0084]

[Table 31]

[0085]

According to the present invention, a good light fastness can be obtained by blending a dye represented by the formula [2] having a similar structure to the dye represented by the formula [1]. , And the temperature dependency and the dyeing property can be greatly improved as compared with the case where each dye is used alone.

Further, a disperse dye mixture obtained by mixing a specific yellow disperse dye and a blue disperse dye with the mixture represented by the above formulas [1] and [2] has excellent light fastness and sublimation fastness, and is very useful. is there.

──────────────────────────────────────────────────続 き Continuation of the front page (72) Koji Tsumura, Inventor 1-1, Kurosaki Shiroishi, Yawatanishi-ku, Kitakyushu-shi, Japan Mitsui Kasei Hoechst Co., Ltd. JP-A-56-18652 (JP, A) JP-A-62-263259 (JP, A) JP-A-47-12585 (JP, A) JP-B-61-39347 (JP, B2) (58) Fields investigated (Int .Cl. ⁷ , DB name) C09B 67/22 D06P 3/54 C09B 29/00

Claims (6)

(57) [Claims] 1. A disperse dye mixture comprising a monoazo dye represented by the following general formula [1] and a monoazo dye represented by the following general formula [2] in an amount of 0.1 to 10 times by weight based on the dye. . Embedded image (In the formula, X represents a nitro group, a cyano group, a methylsulfonyl group or a halogen atom, and Y and Z represent a hydrogen atom, a cyano group,
Nitro group, trifluoromethyl group, halogen atom, or
A methyl sulfonyl group, W is hydrogen atom, a halogen atom, an alkyl group or an alkoxy group of _{C 1 ~C 2, C 1 ~C} 4 alkyl group or a cyano group in R ¹ and R ² each independently represent a halogen atom represents a hydroxy group, hydroxyalkoxy group, C ₁ -C ₄ alkoxy group, hydroxy alkoxyalkoxy group, acyloxyalkoxy group, acyloxyalkyl alkoxyalkoxy group or alkoxyalkoxy C ₂ -C ₄ alkyl group substituted with a group. ) 2. A disperse dye mixture comprising a monoazo dye represented by the following general formula [3] and a monoazo dye represented by the following general formula [4] in an amount of 1.5 to 4 times by weight of the dye. . Embedded image (In the formula, X represents a nitro group, a cyano group, a methylsulfonyl group or a halogen atom, and Y and Z represent a hydrogen atom, a cyano group,
Nitro group, trifluoromethyl group, halogen atom or a menu
Represents a tylsulfonyl group. ) 3. The disperse dye mixture according to claim 1, wherein X in the formulas [1] to [4] is a nitro group. 4. The disperse dye mixture according to claim 1, wherein X in formulas [1] to [4] is a nitro group, Y is a cyano group or a halogen atom, and Z and W are hydrogen atoms. And a disperse dye mixture. 5. A disperse dye mixture 100 according to claim 1, wherein
One part or two or more kinds of yellow disperse dyes selected from the group consisting of the following general formulas [5] to [9] are used in an amount of 2 to 2000 parts by weight.
Parts by weight, and one or more blue disperse dyes 2-2 selected from the group consisting of the following general formulas [10] to [12]:
2,000 parts by weight of a disperse dye mixture. Embedded image (In the formula [5], R ⁵ represents a C ₂ -C ₃ alkyl group substituted with a hydroxyl group or a cyano group; in the formula [6], R ⁶ represents a hydrogen atom, a methyl group or a halogen atom; Medium, R ⁷
Is a hydrogen atom or a methyl group; in the formula [8], R ⁸ is a C ₁ -C ₃ alkyl group optionally substituted by a hydroxyl group or a cyano group; and in the formula [9], R ⁹ is a hydrogen atom or a C ₁ to
Represents a C ₂ alkyl group, respectively. ) (In the formula [10], R ¹⁰ represents a hydrogen atom, a halogen atom, a hydroxy group or a hydroxy C ₂ -C ₃ lower alkyl group,
In the formula [11], A represents an oxygen atom or -NH-;
¹¹ is a lower alkoxy lower alkyl group or a lower alkoxy lower alkoxy lower alkyl group, R in the formula [12]
¹² represents a C ₁ -C ₂ alkyl group, respectively. ) 6. Polyester fibers dyed with the disperse dye mixtures of claims 1 to 5.